


A/S/L

by CrowleyLovesUSUK



Category: Supernatural
Genre: 1990s Crap, Alternate Universe - Human, Alternate Universe - Modern Setting, Alternate Universe - Online Dating, Bottom Dean Winchester, Cas is sort of Awkward, Condoms, Dean is Oblivious about Things., Dean’s First Time With An Actual Human Male, Destiel - Freeform, Dirty Talk, Doggy Style, Explicit Consent, Explicit Language, Explicit Sexual Content, Gabriel Being Gabriel (Supernatural), Humor, Light Spanking, Light dom/sub undertones, Lisa is a Bitch, Lisa is a Cheater, M/M, Mentions of Benny/Andrea, Mentions of Charlie/Gilda - Freeform, Mentions of Past Dean/Bela - Freeform, Mentions of Sex Toys, Moving On, Online Dating, POV Dean Winchester, Past Lisa Braeden/Dean Winchester, Sabriel - Freeform, The Sabriel is background and Not Explicit, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester, dominant cas, fast burn, i think..., mentions of pegging, safe sex
Language: English
Status: Completed
Published: 2019-04-10
Updated: 2019-04-11
Packaged: 2020-01-11 04:26:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 15,372
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18422793
Author URL: https://archiveofourown.org/users/CrowleyLovesUSUK/pseuds/CrowleyLovesUSUK
Summary: When Dean Winchester’s fiancé announced that she was pregnant by another man and walked out, Dean swore off relationships. He couldn’t even bring himself to have casual sex, (which had once been his favorite pastime), with the notable exception of a single eye-opening night. Three years later, Dean’s brother Sam has had enough. A sibling argument leads to Dean signing up for a popular dating site, ‘A Profound Bond.’  When Dean’s first match opens their chat conversation with an outdated query, Dean has to decide if he can move past the other man’s awkward 1990s introduction, and finally take another chance on love.





	1. WTF

**Author's Note:**

> So I was supposed to be working on my other WIPs this month for the April session of Camp NaNoWriMo 2019...but then a friend of mine had something happen. A random (quite young--which made it weirder) guy messaged him on a dating site asking for his a/s/l. What followed from there was a discussion about what kind of person actually asks for that anymore. Didn't a/s/l die out in like 1998--MAYBE 2002 if we have to let it slide for a bit. Either way, my friend was weirded out, and I found myself with a (slightly funny) new idea. This was literally supposed to be about 4,000 words and THAT didn't happen. So whoops! Anyway...have fun. I did.
> 
> A/S/L was old skool 90s Chat Room Speak for "Age/Sex/Location" and in my experience, everyone lied about it anyway because why be 13 and living in a rural farming town in America when you could be 21 and from London or something? There will be other acronyms and slang in this story but they are either explained, or something that I just assume most people have heard before. IDK (That means “I don't know.” 🤣😂)
> 
> WARNING: There are mentions of cheating in this!! Dean used to be engaged to Lisa and she cheated on him and left. It is not specified who she cheated with. Some of the things that follow (including a paragraph that mentions Dean and Bela having a one-night stand) are about Dean trying to get over the fact that he was betrayed in such a way. There is NO cheating between anyone else mentioned in this story.
> 
> I do not own any of the characters in Supernatural (or the show). This is a work of fiction.

Was three years really long enough to get over someone?  As far as Dean Winchester was concerned, he’d move on when he wanted—and not one second before.  Unfortunately, nothing was up to him.

 

His brother Sam said that he needed to shake things up, and warned Dean that at this point, he was just wallowing. Dean still lived in the same apartment he’d shared with Lisa.  He’d kept the same routine; going to bed at the same time and driving the same route to work. Literally _nothing_ in Dean’s day-to-day life had changed much since the night that Lisa had told him she was pregnant and that the baby wasn’t his.  In his own way, Dean felt that if he didn’t change anything, then maybe it still wasn’t his reality. He was lucid enough to know how fucked up that way of thinking could be, and he didn’t care.

 

Sam did.

 

They had fought, one drunken night last month, and Dean had caved at the damn puppy eyes that his brother had perfected. Sam said that he needed to move on, so that’s what Dean would do. He’d do anything to get Sammy off of his fucking back. His brother had to concentrate on grad school—not waste time on _his_ sorry ass. So Dean gave in and said that he’d try dating again. Sam had laughed grimly and said that dating was beyond his expectations and that he’d just be happy if Dean got laid at this point.  That had stung.

 

He’d tried after Lisa walked out. Truly tried.  He’d actually went out to the bar that night after she’d left with... _him._ Sam and Benny had practically dragged Dean out, looking for a rebound. But all he could see were flashes of his fiancé in the random people who chatted him up. It made for shitty conversation, and Dean hadn’t blamed any of them for moving along and leaving him to his broken heart. He’d been way too much drama for a simple hookup back then.

 

Two months after Lisa left, he ran across a picture of her on his social media showing her and _him_.  It was an announcement photo, professionally done. The dickbag’s arms were around her, holding Lisa’s protruding belly and they’d been smiling. Dean actually ran to the bathroom and dry heaved before deleting her profile from his ‘Friends.’  That night, he’d called Gabe.

 

Gabriel Novak was Sam’s best friend, roommate, and, Dean suspected, his FWB, too.  Sam didn’t kiss and tell, but the two of them were _way_ too handsy to be ‘just buddies.’  No one made out with their _platonic_ same-sex friends when drunk, in Dean’s opinion. Either way, Gabriel was exactly what Dean had needed after _that_ fucking debacle online. Gabe was a fucking force to be reckoned with, and Dean knew that he’d end the night either black out drunk (goal), or in bed with someone hot and willing (plus).

 

Thankfully, Gabe had left Sam at their place and showed up alone to take Dean out that night. Due to the short blonde’s effervescent personality and his connections, two hours later, Dean was on his way to hammered and getting into an Uber with a sexy brunette named Bela.  The last thing that Dean remembered about that night was Gabe shoving a condom into his palm and telling him to “have fun,” before slamming the car door and waving.

 

Waking up the next morning, naked, in a strange bed and a sharp pain in his ass had been a bit of a wake-up call. Bela had been kind enough to explain—after another round—that she had a thing for pegging and that Dean had been ‘all for it’ the previous night. Surprisingly enough, the rising ‘gay panic’ that Dean figured was on its way never appeared. He was shockingly fine with the whole experience. His late father may have thought that ‘butt-stuff’ was gay; but Dean had been doing it with Bela, who was _obviously_ very female. He and Bela had exchanged numbers and the sexy British girl had been very clear that Dean was welcome in her bed _anytime_.  He’d meant to call her, but he never had.

 

The night with Bela and her strap-on had been a bit of a wake up call for Dean who figured that now was as good a time as any to explore his sexuality. He’d kept a firm lock on his closet door since puberty.  But there was nothing like your wife-to-be getting knocked up by another man to make someone realize that there were all kinds of ‘secret shame.’

 

His parents were both dead--grandparents too, for all Dean knew. He’d never known of any extended family, so he began to wonder—who the _fuck_ was he trying to hide from?  No one. The ache in his ass for the next few days gave Dean the push to discreetly purchase a rather thick vibrator online, and he’d never looked back.

 

For the first time in his life, Dean Winchester had felt free. He experimented and researched—something that was more his brother’s style. He’d maxed out a whole paycheck on the ‘Naughty Niceties’ website (we deliver in unmarked packages—wink).  A year after Lisa had left, Dean met Sam for beers and told his younger brother that he might be ‘sort of gay.’

 

Unsurprisingly, Sam was fine with it. He’d come busting out of the closet one month into his freshman year of college.  Which was another reason why Dean suspected that Gabriel was a little more than a BFF to Sam. The little guy was _exactly_ Sammy’s type, and—as he’d thought—they touched each other...a lot...in not strictly _friendly_ places.

 

Dean had almost left when Sam had suggested a few other brands for toys as well as a couple porno titles that Dean might enjoy. His brother meant well, but Dean really didn’t need _that_ much support.

 

For the next two years, Dean had ‘moved on’ as best as he could. He had his toys, he’d experimented enough to know _exactly_ what he liked, and he was about ninety-nine percent certain that he liked cock—a lot. He had thought that he was doing well. That is, until Sam pointed out that Dean hadn’t dated since Lisa’s betrayal. Sammy had also said that ‘a single one-night stand in three years’ wasn’t enough to qualify as ‘moving on.’  That was the night they’d fought.

 

Dean fucking _hated_ fighting with Sam. They were family—almost closer than close.  The second that their voices even raised, Dean was ready to give in to whatever Sam wanted.  Apparently what Sammy wanted was his brother’s happiness. He’d promised Sam that he’d _try_ and kicked his brother out to go touch his hyper roommate.

 

The next morning, Dean woke up and groaned, remembering. Fuck. He waffled about it while showering and brushing his teeth, trying to figure out how to weasel out of things before he finally just decided to fuck it all. If Sammy wanted effort and change, then Dean would bring it like a boss.

 

It was nine am and Dean cracked open a beer, settled into his recliner and turned on his cell phone. He would join a dating site and see what happened. For Sam, of course. He’d show his little brother that he wasn’t a weird shut-in who was ‘totally satisfied’ with his now impressive array of toys. Sometimes he was happy; but there was that persistent ache for someone to just _hold_ him.  He’d never fucking tell Sammy—or anyone— _that_ bullshit though. He might be more into dick at this point in his life, but that didn’t mean that he was about to cry about his sad and lonely feelings.

 

For a moment, Dean considered who to ask for help.  Sam was out, for sure. Gabriel would probably suggest something perverted and out of Dean’s comfort zone.  Benny wouldn’t have any idea, since he’d been dating Andrea since fifth grade. That left Charlie.

 

Taking a moment to mourn the loss of his previously uncomplicated life, Dean finally called his surrogate little sister. Charlie answered on the second ring with a, “Sup, bitch!  This better be good, because I think I found a previously undiscovered Easter Egg in ‘Shadow of the Tomb Raider.’”

 

“I’ll be quick, and it’s important,” Dean promised.

 

He could hear something scratching near the phone and a loud thunk before Charlie said, “I’m all ears, Skywalker.”

 

“Sammy thinks I’m still wallowing about the...well,” Dean shrugged before he remembered that Charlie couldn’t see him.

 

“The Lisa Incident,” his normally sweet friend growled bitterly. Dean knew that if Lisa ever showed up again that Sam would be the first in line to ream her out verbally—but Charlie would most likely throw a punch. His lil’ sis had taken the whole thing _very_ personally. Dean and Charlie had been friends since elementary school when they bonded over a shared love of Star Wars and Super Nintendo—and they had weathered many a storm. He knew that Charlie wanted to gouge out Lisa’s eyes, and possibly drink mead from the cheating bitch’s skull (if that weren’t slightly creepy and unsanitary).

 

“Yeah,” he said after he’d allowed Charlie to mutter a sting of inventive curse words. “He and I kind of got into it last night. Long story short, I promised to get back in the saddle, as it were.”

 

“Dean!” Charlie gasped. “You said this was important—you didn’t say that this was basically life and death!”

 

“You’re being dramatic,” Dean rolled his eyes.

 

“No,” Charlie said. “I’m toning shit down because _you_ are allergic to feelings. But,” she shrieked like a fucking dinosaur into the phone, “this is _amazing_!  What can I do?”

 

“I don’t want to double date just yet,” Dean told her. “And I’m just looking for casual right now.”  He wanted to be crystal clear because if Charlie got going, he’d likely find himself married in Vegas to someone they LARPed with. “What was that dating site that you met Gilda on?”

 

“It’s called, ‘A Profound Bond,’” she said. “You can google it or I can message you a link.”

 

“I’ve got it,” Dean said. “Thank you, My Queen.”

 

“Anytime,” Charlie’s voice was deceptively casual. “They match you based on personality and shit—first and foremost. I mean, yeah,” Charlie sighed and Dean could picture the dreamy look that she had whenever she mentioned her wife. “They take into account physical traits that you appreciate or desire, but it’s really for an emotional connection.  It’s not actually a _casual_ sort of dating site.”

 

“It’s fine,” Dean said. “I said casual, but I really don’t care. I’m doing this for Sammy, but I don’t want to end up with someone like... _her_...again, you know?”

 

“Ten-four,” Charlie said. “Okay, you get signed up and I’m going to see if this code I figured out will make Lara Croft topless.  You just tell me when you want to double date, and Gilda and I will be there with garters on. Not for you though—for us. Later.”

 

“That’s a creepy image that I didn’t want,” Dean muttered.

 

Charlie was an attractive women, for sure!  But he absolutely did _not_ think of her that way. She was like a Barbie to him—no... _parts_.  Her wife was the same. Gilda was movie-star hot—but no. Adding on to that, both of them were strictly into the ladies, and Dean felt kind of weird picturing them in their panties. Like he was objectifying lesbians or something. He wasn’t entirely sure. Sam had went off about it one night and it just weirded Dean out enough that he’d blocked all previous mental images of Charlie and Gilda out of his brain...forever.

 

“Bye,” he hung up and leaned back into his chair.  Well, it was now or never. Dean had basically announced to his group of friends that he was going to get back out there now. If Sam and Charlie knew, he may as well have rented a fucking billboard.

 

He changed the channel on his television and debated on doing the dishes by hand for a while to postpone the inevitable. However, once Dean put his mind to something, he followed through. Eventually he searched for the site and soon enough he was making a profile on ‘A Profound Bond.’

 

It took a ridiculously long time and some of the questions were almost downright embarrassing. He even had to take some pictures to upload that would prove he was accurately describing his ‘physical attributes.’  That meant selfies, because Dean lived alone and wasn’t very creative. He fucking _hated_ selfies. He’d even scrolled through his social media accounts and out of the few pictures of him, none were close enough for the ‘Portrait’ that the stupid site required. The only one passable was actually a picture from years ago of Dean and Lisa.

 

He’d been beyond pissed when he stumbled across it. He had been so certain that he’d purged all of those after that one night with Bela the Pegger.  Apparently he’d missed one. Instead of making him second guess his actions as he looked at the happy smiles in the picture, it had solidified his resolve. He’d thought that he’d been happy then—the timing showed that Lisa was probably already fucking knocked up when the photo had been taken. Dean deleted it and immediately went back to be a little more in-depth and honest for some of the dating site’s queries.

 

Almost two hours later, Dean flopped back into his recliner with a sigh. His ass was numb from sitting for so long and he was still gritting his teeth whenever he remembered that last photo of him and Lisa. He’d also managed to make a dent in his beer stash while he’d been registering as a single man looking for love online.  The automated email he received moments later informed him that “Love was Coming” (in five to seven business days). Okay then. That was that.

 

He didn’t have anything better to do, and it was almost lunchtime, so Dean pulled on his jacket, grabbed his wallet and left.  His regular bar, The Roadhouse, was only a short walk from his place—hence his regularity. He could grab a burger and maintain his morning buzz, with the added benefit that his friend Benny was a chef there, and Dean needed a Cajun Burger like he needed air.

 

Forgoing a table, Dean slid onto a bar stool when he arrived.  The bartender, Ash, wandered over to him and placed two shots (bourbon and whiskey) and a pint of IPA without a prompt. “Food?” Ash was a man of few words.

 

Dean nodded and Ash made an odd twitch with his shoulder. Dean nodded again and Ash walked back toward the window leading into the kitchen. “Benny!  Cajun burger, medium, extra spice, extra cheese, no tomato, double fry, double coleslaw!”

 

He smiled when his friend poked his head out and said, “Didn’t think I’d be seeing you today, brother!  Coming right up—I’ll fry you up and come out for a drink.” Dean gave Benny a salute and wondered if it was odd or pathetic that he had a regular order at a bar.

 

He polished off the beer and both shots, along with another round before Benny came out, carrying Dean’s lunch. “Dear sir,” Benny’s thick drawl sounded insanely hilarious in the weird French accent he was trying to imitate. “I do hope that your meal is up to your high and illustrious standards.”

 

“Fuck off,” Dean laughed as his friend dropped the plate in front of him and sat down.  Dean had his priorities and took a few large bites of his burger before utilizing his words. “Fucking amazing, as usual,” Dean said through an indecent moan and a mouthful of perfectly done beef.  He stuffed a few crispy fries into his mouth before it happened.

 

“Heard you were joining a dating service,” Benny sounded casual, but Dean knew better. His buddy _wanted_ the gossip first hand. Needed it.

 

“Who told?” Dean really didn’t care.

 

“Gilda said something to Andrea at work,” Benny shrugged and stole one of Dean’s fries. “I am so talented, I don’t even know what to do with myself,” Benny hummed as he chewed his own cooking.

 

Of course. It had literally been _almost_ three hours by now. Dean told Charlie, and _of course_ she had texted her wife. Gilda and Andrea worked the same weekend shift at the hospital and were friends. And Andrea rivaled Sam and Charlie for the title of the reigning gossip queen of their group. Dean honestly wasn’t surprised.

 

What _did_ surprise him was the sudden buzz and alert from his normally silent phone as it sat on the counter of the bar between them.  Dean checked the notification and saw that it was from the dating app. He figured that it was most likely some sort of welcome message, but he decided to look anyway.  It turned out that it wasn’t a greeting at all. It was a match!

 

Dean looked up at Benny and blinked. “They said that it would be a few days,” he sounded stunned.

 

“Maybe this one is meant to be?” Benny shrugged and moved to head back into his kitchen. “You have fun, brother.”

 

Dean nodded and looked at his phone once more.  The new match seemed to be staring at him. The blue dot told Dean that the man had blue eyes, which was his personal weakness. The short list of stats seemed promising as well. Only a year older than Dean and confirmed employment. So far so good. Dean pulled up the chat box for his match. The provided moniker said ‘Angelus_Iovis,’ which meant nothing to Dean.

 

**Impala67: Hey!**

 

He really wasn’t sure what else to say. The site matched potential couples based on the questionnaire, but they didn’t give away much information on a match.  All that had been provided for Dean on this Angelus dude was the eye color, age, confirmation of a job, and a vague location—meaning that this man apparently lived within twenty-five miles of Dean.  

 

The tiny chat bubbles popped up, indicating that his match was about to respond. Dean was surprised at how anxious he felt. A few minutes passed and nothing came—Dean was impatient. He began to fidget with his phone until _finally_ a message came through.

 

**Angelus_lovis: a/s/l?**

 

Wait. What?  Dean reread the message and shook his head. Had he accidentally been transported back in time to the 90s?  Was he communicating with this dude on the AIM Messenger right now? What in the fuck was going on? Did anyone even _ask_ ‘a/s/l’ anymore?  And barring all of Dean’s rushing questions—all of those queries could be answered by looking at his profile.

 

He had to admit that he was curious and wanted to ask the other man if it was a joke or a legitimate question.  As usual though, Dean’s stubbornness won out and he simply closed the app without responding. That was fucking weird and Dean had enough to deal with at the moment. He would wait until another match came through.

 

* * *

 

Two days later, Sam had called, all excited about Dean’s match. He didn’t bother asking how his brother had found out. Benny to Andrea to Gilda to Charlie to Sam—and most likely Sam to Gabe. He expected that by now all of their friends knew. Not wanting to burst his brother’s bubble by admitting that he still hadn’t responded to the guy, Dean found himself agreeing to a movie marathon that night at his brother’s place.

 

Dean showed up with a few six packs of a new local brew for him, a bag packed full of candy for Gabriel, and a single kiwi for Sammy.  His brother gave him a bitchy look when he passed the small fruit over with a laugh. “Thanks, Dean,” Sam rolled his eyes. “So nice of you to bring by _one_ random piece of fruit.”

 

“My pleasure,” Dean chuckled, following Sam inside.

 

Gabe was sprawled on the couch trying to take up as much room as possible.  Dean threw the bag of treats into Gabe’s stomach and laughed when the smaller man immediately sat up to dig through the goodies happily. He took his usual chair and watched as Sam maneuvered onto the couch behind his roommate and pulled Gabe between his legs. Dean wasn’t sure who Sam thought he was fooling, because no one snuggled on a sofa like that if they weren’t into the other person. It also seemed like something that was a regular occurrence since Gabriel just settled back into Sam’s chest without a word, clutching his candy, and giving Sam the sappiest fucking look of all time.

 

“Are you sure you two aren’t dating?” Dean finally asked the question he’d been thinking about for _years_.  

 

Both men stared at Dean before looking at one another and practically giggling.  Gabriel shook his finger at Dean, chuckling loudly. “That’s funny, Dean-o.”

 

“What?  Why?” Dean grabbed one of the beers and looked confused.

 

“Are you serious?” Gabe wrinkled his nose and then shifted to look up at Sam. “Is he joking?”

 

Now Sam was eyeing him looking lost. “Dean,” his brother said.  “You know that.”

 

“Know what?”

 

“Oh, holy fuck,” Gabe clapped his hands and started laughing again. When he managed to control himself he looked at Dean and said, “Sammy and I have been living together for five years.”

 

“I’m aware,” Dean sipped his beer.

 

“Dean,” Sam said. “Gabe and I started dating about two hours after we met. We didn’t move in together as roommates—we moved in together as a couple.”

 

Blinking stupidly, Dean said, “but you have a two bedroom place?”

 

“Yeah, for you, you giant moron,” Gabe laughed. “Sammy wanted a place that you could move into in case anything ever happened.”

 

“The second bedroom is set up for a guest,” Sam nodded. “For _you_ , mostly.”

 

“Although it should be getting lots of use at _any_ moment,” Gabriel didn’t clarify his statement in any way before sobering and giving Dean a weird look.  “We almost offered after Lisa,” Gabe told him. “But Sammy didn’t want to push you.”

 

Dean’s head was swimming. He’d suspected something was going on with Sam and Gabe for years, but he’d never really thought that he was so far out of the loop that he didn’t realize his brother was practically _married_!  The first thing that came into his mind was, “What the fuck?”

 

“Wow Dean,” Sam said with an awkward laugh.

 

“I knew you were pretty obtuse,” Gabe chimed in, “but I honestly thought you knew.”

 

“I had my suspicions, but you two never _actually_ said anything,” Dean pointed out.

 

“I’ll be sure to make things super obvious with my next boyfriend,” Sam said as he leaned down to give Gabe a sloppy kiss.

 

“Next boyfriend, kiddo?  Really? You know how crazy it makes me when you’re a tease.  Don’t make me spank you,” Gabriel teased lightly and kissed him back.

 

“Gross,” Dean groaned. “I can handle the cuddling and the weird touches because you two have been doing it forever—but can you try not to swallow my brother’s tongue in front of me?”

 

“No promises,” Gabe smirked.

 

They started their chosen movie and settled in.  Occasionally one of them would make a comment or observation about the film, but they mostly watched quietly.  Even Gabriel managed to shut his pie hole for the majority of the movie, which was a minor miracle.

 

A break was called between films and Dean found himself standing in the kitchen watching Sam mix up some sort of dip for his giant bowl of veggies. He was pretty sure he’d seen Sam pour sawdust in, and he wrinkled his nose. “You do realize that when you die, you’ll regret all of the delicious foods that you could have eaten but never did?”

 

“I’m perfectly happy with my choices, Dean,” Sam was used to the argument and just smiled at him. “So, you haven’t told me about this guy—the one you were matched with.  What’s he like?”

 

He couldn’t deflect such a direct question too easily, so Dean considered his options. He could be honest— _or_ he could just make the guy sound like a jerk and Sam would drop it. Before he could open his mouth, Gabriel joined them—and he was looking at Dean’s phone.  “I can’t tell if this is a joke, or dead serious, but either way, I love it!”

 

Dean lurched and grabbed for his phone. Gabriel was quick and jumped behind Sam and out of reach. “Damn it, Novak!”

 

Gabe was now squished between Sam and the counter and showing the phone screen to his boyfriend. “Is that not the weirdest opener?”

 

“You haven’t messaged him back?” Sam looked up from the phone to Dean. He had the fucking puppy eyes and Dean groaned. Shit.

 

“Dean-o, you _gotta_ message back,” Gabe insisted. “I need to know what kind of a person still uses ‘a/s/l’ as an ice breaker.”

 

“Wait, what?” Sam finally looked back at the phone and read the chat that Gabe was aging at him. He laughed, a short chuckle blowing through his lips before he schooled his features and met Dean’s gaze. “He seems nice.”  Sam’s voice was oddly pitched and Dean knew his brother’s fake serious expressions better than anyone.

 

“Shut up, bitch.”

 

“Jerk.”  

 

“I’m not going to respond,” Dean finally said after a minor stare-down. “He’s obviously a weirdo.”

 

“What?  Like you’re not?” Gabe snorted as Dean flipped him off.

 

Sam took the opportunity to speak up. “Maybe he’s just not very technologically savvy...like _you_.”

 

“What?” Dean protested. “I’m can do...tech...stuff...just fine!”

 

Both Sam and Gabe raised their eyebrows at him and the effect was unsettling. Jesus, they had each other’s mannerisms—how had Dean really not known they’d been official?  “Dean, you had a flip phone up until a year ago. I honestly didn’t even know that those things were still being sold,” Sam said.

 

“My phone was perfectly fine for what I used it for,” Dean grumbled.

 

“But it’s much nicer to have one that you can watch porn on wherever, and whenever, you want, am I right?” Gabe asked.  The two brothers glared down and him and he made a face. “Wow. Just me. That’s weird.”

 

“Anyway,” Sam rolled his eyes at Gabriel before turning back to his brother. “Just because he uses outdated chat speak doesn’t mean he’s creepy. You’re both about the same age and he might have been doing it as a joke since you would both have used AIM and all that crap growing up.”  

 

Dean blew out a breath. Sammy might have a point. Plus, they had been matched so quickly and the site was known for setting up people who were truly compatible.  Maybe Dean _had_ been to hasty and judgemental by not responding.

 

He snatched the phone from Gabriel while the shorter man was distracted and making sappy faces at Sammy.  Before he could second guess himself, Dean began to type.

 

**Impala67: All of that is in the profile that was sent to you, Dude.**

 

Looking up from his phone, Dean was treated to the _wonderful_ sight of his brother making out.  Which he didn’t need to watch. Dean made a disgruntled sound and the two lovebirds broke apart.  Sam looked dazed and Dean glared at Gabriel. “Don’t do that,” he pointed at both of them. He was about to suggest that they start the next movie when his phone chirped.

 

**Angelus_lovis: I am aware of that now.  My apologies.**

 

Dean hummed thoughtfully.  Okay—so the guy was a bit formal, Dean didn’t mind that. And he knew that his opener had been weird. Dean was inclined to give this guy a shot.

 

**Impala67: So, Angel?  What are you looking for?**

 

**Angelus_lovis: This is a dating site. I am looking for dating. And why did you call me Angel? Do we know each other?**

 

Dean blinked.  This guy was apparently a bit more than eccentric, but for some reason, Dean wasn’t quite ready to let go.

 

**Impala67: Dating is good. And I’m pretty sure I don’t know you. I called you Angel because of your screenname.**

 

**Angelus_lovis: Oh, yes. That does make sense. It’s refreshing to meet another person who knows Latin.**

 

He chuckled to himself. Sammy was the one who took Latin in school. Dean just picked up random things here and there helping his brother study. If it managed to impress someone, then Dean would consider it time well spent. He was about to respond when another message popped up.

 

**Angelus_lovis: Perhaps we could meet F2F?**

 

Oh fuck, really?  Dean had to search the dark recesses of his mind to remember that one at first.   _F2F_...oh, right…’Face to Face,’.  What fucking year was this guy living in, honestly?  In for a penny and all that—Dean decided to throw in an obnoxious acronym of his own.

 

**Impala67: Sure. We should definitely meet IRL.**

 

**Angelus_lovis: I am not familiar with that.  IRL? It’s not on my list.**

 

List?  Dean was intrigued. What exactly did that mean?  He quickly typed out a query and waited anxiously for his Angel to respond.  Woah—when had he started thinking that this apparently nerdy, stuck-in-the-90s guy as ‘his?’

 

**Angelus_lovis: My brother supplied me with a list of things that people say online so that I would fit in better. I don’t use the internet very often, if I am honest.**

 

Dean closed his eyes and his mouth dropped open in realization. That poor fucking guy.  His brother was a _dick_ —Dean could relate to sibling bullshit though.

 

“What’s wrong?” Sam asked, and Dean realized that they were all still hanging in the kitchen.

 

He turned the phone and showed the conversation to Sam and Gabriel. When they finished reading, Gabe was laughing and Sam looked bemused, yet also disturbed.

 

“That is...really terrible,” Sam finally said as Gabe cackled behind him. “And childish.”

 

“Which means it’s something that Gabe would do,” Dean said.

 

Gabriel’s mirth trailed off and he confirmed, “I would _absolutely_ do that.  It’s fucking hilarious.”

 

“Because you’re basically a child,” Sam teased.

 

“Hey, I’m older than you, kiddo,” Gabe protested.

 

“But you _are_ the same size as a child,” Dean laughed.

 

Gabe glared.  “Fuck you, Winchester,” but there was no venom behind it.  “So? Are you going to meet him? F-two-F or IRL?”

 

“Don’t talk like that,” Sam requested, shaking his head.

 

“You know,” Dean said, opening another beer.  “I think I will.”

 

**Impala67: You name the time and place, Angel.**

 

He ignored Gabriel’s knowing smirk as they continued with their evening. Gabe usually looked like a smug little shit, so it most likely didn’t mean anything...not anything at all.


	2. F2F

**Notes for the Chapter:**

> This is the NSFW chapter. Things get a little dirty. Cas is a bit dom, and Dean discovers that he likes it. A lot!

‘Angel’ got back to him almost an hour later, suggesting a diner that was actually only a few blocks away from Sam’s house. He mentioned that he was new in town and that his brother had recommended the place. Dean wondered if it was the same brother that was messing with the guy.  If so, then the brother might be a dick, but at least he had good taste in food. 

 

Dean thought that they should meet up that Friday evening, which was readily accepted by ‘Angel.’  By now, Dean’s attention was completely on his phone and not the movie—or the fact that Gabe and Sam seemed to be eating each other’s faces on the couch.  Dean definitely wasn’t noticing  _ that _ horrifying spectacle.  He settled in, hoping that the two of them could chat a bit, but a new message came through that dashed Dean’s hopes. 

 

**Angelus_lovis: I must get back on the road. I don’t actually arrive in town until tomorrow.  I look forward to meeting you on Friday. TTFN.**

 

Dean honestly couldn’t remember what  _ that one  _ meant. He cleared his throat, forcing Gabe and Sam to unglue and asked them. “It means ‘Ta, Ta For Now,’” Gabe told him. 

 

“Oh yeah,” Sam nodded. “What Tigger used to say.”

 

“Yup,” Gabe chirped. 

 

“Who?” Dean asked. 

 

“Tigger?  Winnie the Pooh?  House on Pooh Corner?  None of that rings a bell?” Gabe actually looked shocked. 

 

“Yeah, we really didn’t have the kind of family that read us bedtime stories,” Sam said softly. 

 

“Oh, right,” Gabe said. “Fuck, I’m sorry, kiddo.”

 

“It’s a kid’s book?” Dean spoke up, because it looked like those two were about to start the kissing bullshit again. 

 

“Yeah,” Sam nodded. “It’s good.”

 

“You two are weird,” Dean told them. 

 

“Says the man who read ‘Twilight’ with my boyfriend,” Sam laughed. 

 

Both Dean and Gabe grumbled. “It was for a book club,” Gabe said. 

 

“A book club for just the two of you and Benny?  Right, okay,” Sam was fully chuckling now. 

 

“Whatever.  It was compelling,” Dean said grumpily. 

 

“I was Team Edward,” Gabe said.  “Dean-o was all about the werewolves, but Benny took my side. Although he said the book wasn’t bloody enough for him.”

 

“No one is surprised by any of that,” Sam told them.  “I take it that you’re going to meet up with this guy then?”

 

“Friday,” Dean nodded. “He wants to go to Donna’s.”

 

“At least he has good taste,” Gabe said. 

 

Sam looked thoughtful. “A lot of the customers at Donna’s are people from the neighborhood,” he said. “We might actually know this guy.  I mean, we’re there all the time.”

 

“Nah,” Dean waved a hand. “He said he’s new in town and his brother suggested it. He’s not actually even rolling in until tomorrow.”

 

Sam’s eyes narrowed and he shot a glance at Gabe. “Oh, really?”  The timbre of his voice was suggestive—as though Sam had just figured something out. 

 

“I’m sure he’ll be happy to have you showing him around town then, buddy,” Gabe said quickly.  “Is he going to get the tour of your nether regions as well?”

 

“You’re psychotic,” Dean told his friend.  It was something that Dean said about his friend quite often. 

 

“Gabriel?” Sam rarely used Gabe’s full name and it made both of them stop and pay attention. 

 

“Nope,” Gabe shook his head and stared hard at Sam. 

 

Dean watched as the two of them had a silent conversation with their eyes. Eventually Sam shook his head and huffed, “Whatever.”

 

His brother turned the movie back on and they all settled in to finish. Dean had a feeling that he should have pressed on whatever was going on between his brother and Gabriel, but he just didn’t have the energy. Despite the fact that Angel had said he would be driving for a while, Dean found himself almost obsessively checking his phone for the rest of the night. 

 

* * *

 

For the first time since possibly Lisa’s departure, Dean was looking forward to the weekend. Being single, and still bitter over his last relationship, Dean didn’t have the best experience with free time. His coworkers loved him, because he was always willing to stay late or cover shifts. If he was busy, then he wasn’t thinking about all of the ways he could have done things to make Lisa stay faithful. His friends all told him regularly that she would have done it no matter what because “cheaters are cheaters, Dean.”

 

This Friday though, Dean was going to meet his match—possibly the man of his dreams—and he couldn’t wait. The time both dragged and flew by, which was unnerving. When the end of his shift arrived on Friday afternoon, he shouted goodbye to Bobby and headed to his apartment to get ready. 

 

He opened a beer as soon as he walked through the door to try and calm the roiling feeling in his gut. It wasn’t butterflies, because he was a grown man and adults didn’t get all gooey over a date. At least, Dean didn’t.  When he got to his bedroom, he stopped in the doorway and stared at the pants and button down that were folded neatly on the bed. Those had  _ not _ been there that morning. 

 

Just as he stepped into the room, his phone chimed with an incoming text.

 

**From Gabe (Tr1ckster): I know that you think flannel is sexy AF, but most MLM aren’t super into dudes who dress like a straight boy from Canada. I picked out your clothes. Wear them. You’ll thank me. Good thing Sammy and I have a key to your place, huh?**

 

Dean rolled his eyes as he read the message. He loved Gabriel, but the man had zero boundaries. Especially now that they were practically in-laws.  

 

**From Me (Batman): Dude, you’re psychotic. Stay out of my house. That key is for emergencies only.**

 

**From Gabe (Tr1ckster): Your wardrobe is an emergency.**

 

Grumbling as he looked over what Gabe had picked, Dean realized that his friend had chosen an outfit that would accentuate his best features.

 

**From Me (Batman): Fuck off.**

 

**From Me (Batman): Thanks, Gabe.**

 

**From Gabe (Tr1ckster): Go on and part the Gates of Mordor.**

 

**From Gabe (Tr1ckster): Go get his dragon in your dungeon.**

 

**From Gabe (Tr1ckster): Have him put his wand in your Chamber of Secrets.**

 

**From Gabe (Tr1ckster): Get you some butt sex!**

 

**From Me (Batman): Don’t ever speak to me again.**

 

**From Gabe (Tr1ckster): Love you too, buddy!**

 

Glancing at his watch, Dean hurriedly dressed in the clothing Gabriel had picked—he didn’t want to be late. As much as he had tried to convince himself that he was just doing this for Sammy, Dean couldn’t help but wonder if this was going to be his  _ last  _ first date. 

 

“Don’t be a dumbass, Winchester,” Dean muttered out loud. It would be dangerous to let his guard down. He’d settled into a comfortable life with Lisa, and look how  _ that _ had fucking turned out.

 

He absolutely did  _ not  _ check his hair three more times as he made his way to the front door. Okay, so maybe he did—sue him!  When he absolutely couldn’t wait any longer, Dean grabbed the keys to his 1967 Chevy Impala—the  _ actual _ love of his life—and headed out. He forced himself not to think of the newly purchased condom that he had stuffed into his pocket after Gabriel’s annoying texts. 

 

When Dean arrived at Donna’s Diner, the woman herself greeted him with a “hey how are ya” and a huge bear hug. Dean was a regular and he not only loved the food there, he genuinely adored Donna Hanscum. 

 

In another life she’d been a small town sheriff, but she had packed it in for reasons unknown. She always told Dean that she’d turned in her badge, (just like in the movies), got into her car with one suitcase, and started driving. She’d ended up here and bought the old corner store that the city had been ready to tear down. Just under a year later, the diner had opened—and thrived. 

 

Dean used to come with Sam and Gabe all the time. He’d been less frequent when he had been with Lisa because she only ate macrobiotic, (whatever the fuck that was).  But since his cheating lover had walked out, Dean was parked in a booth at Donna’s at least once a week. He was honestly surprised that Gabe could convince Sam to eat there, due to his little brother’s penchant for an ‘organic only’ diet of salads. But Gabriel had always been able to make Sam do things out of the ordinary. Maybe that's why they worked so well together. Dean was still reeling that he’d been kept out of the loop on Sammy’s love life—he had plans to make Gabriel pay for that little omission.

 

“I am super excited to see your cute fanny here!” Donna beamed at him. “Where’s the Terrible Twosome tonight?  They meetin’ ya?”

 

“Nope.  Sam has a paper due and I think Gabe wants to make sure he takes regular breaks.”  Donna snorted at that. Apparently she’d figured out the relationship status there before Dean.  He paused for a second and tried not to show his enthusiasm. “I have a date.”

 

“Oh—Sweet Valley High—you don’t say!”  Donna rarely swore more than a well-placed ‘crap,’ and Dean was consistently amused at what phrases she managed to come up with on the fly. She pulled him into another bruising hug before leading him toward the corner booth. “You need The Matchmaker tonight,” Donna told him. 

 

He tried to protest. The corner booth was a very sought-after spot at Donna’s due to the uncanny way that couples who ate in it, would be married within six months. Donna had nicknamed the table ‘The Matchmaker’ and was very particular about who was allowed to sit there. The local news had even done a story on the table, increasing the diner’s popularity. 

 

Donna physically moved him so that he was plopped down into the squashy cushions of the booth and Dean just gave in and let her do her thing. “There,” Donna clapped her hands and smiled at him. “You look so handsome and I’m sure that this old table will work it’s magic for you,” Donna winked. “Or at least help you have a little fun between the sheets, am I right?”

 

“Donna!” Dean wasn’t embarrassed by the implication, he was more shocked that, of all people,  _ Donna Hanscum _ was the one making it.

 

“Please, Dean,” Donna swatted his shoulder. “I’ll have you know that in college they called me ‘Dirty Donna!’”

 

“Okay, I didn’t need to know that,” Dean told her, making a face at her teasing.  Donna wished him luck and bustled away.

 

Dean sat alone in the booth, waiting. He wasn’t worried since he’d managed to arrive almost twenty minutes before they had planned. He didn’t need to look over the menu, and he honestly  _ hated _ staring at his phone, but he could see the sidewalk and the occasional pedestrian through the window to his right, so Dean busied himself with people watching. 

 

A few minutes passed by when suddenly Dean’s attention was caught by a rather tall, dark haired man walking down the street. Dean’s gaze first fell onto the broad shoulder that were almost pulling at the seams of the boxy trenchcoat that the guy was sporting.  As the man came near, Dean actually licked his lips at the sight of the disheveled hair and the trace of stubble along the guy’s jaw. His features looked almost upset, but the ‘freshly fucked’ look was doing a  _ lot  _ for Dean. Enough that he squirmed in his seat. 

 

As the man moved away, Dean wished that the coat was shorter so that he could get a glimpse of what he was sure would be a sinfully tight ass.  Dean shook his head as the guy turned out of sight and hoped that his date was at least half as attractive as Mysteriously Hot Trenchcoat Dude.

 

The bell to the diner rang and Dean could hear Donna greeting someone.  He couldn’t make out the words, but a deep voice responded to her and Dean perked up a bit. Was this his date?  He leaned a little out of the booth, and his mouth dropped open when he saw Donna heading his way with Hot Trenchcoat Guy!  

 

Donna gestured to the booth with a saucy wink at Dean as the man slid in and said hello.  “My apologies if I’m running late,” he was saying. “Are you ‘Impala67?’”

 

Dean gulped and blinked. Those  _ eyes _ !  He hadn’t seen the fucking  _ eyes _ while the guy walked by. Holy shit—they were like the freaking ocean. So blue and inviting; and Dean  _ did _ have a weakness for baby blues.  He saw that the guy was edging back out of the booth looking uncomfortable and Dean finally said, “Where are you going?”  He didn’t even flinch at how desperate he sounded. 

 

“I assumed that I had been seated at the wrong table,” the man said.

 

“No!” Dean shouted. “No,” he lowered his voice and waved his hand to try and get the arguably hottest guy he’d ever seen to sit back down.  “Sorry, I was distracted. I  _ am  _ ‘Impala67,’ but you can call me Dean.” He paused awkwardly at the silence. “That’s my name. Dean. That’s why...you can...call me that.  Ah, fuck.” Dean dropped his head into his hands. Wow. Piercing blue eyes and sexy hair, and suddenly he couldn’t string together a coherent sentence—awesome.

 

When Dean looked back up, the other man was looking at him curiously.  “Hello, Dean.” And if that throaty voice saying his name didn’t give him a partial boner; Dean felt like a damn teenager. “My name is Castiel.”

 

When Castiel held out his hand very formally, Dean didn’t hesitate to grab it and shake—anything to initiate touch with this man.  “Wow,” was all that Dean could come up with. 

 

Their hands stayed clasped together much too long to be anywhere close to normal.  Dean wasn’t even sure when they simply set their still entwined fingers in the table instead of letting go.  He had no idea how long they stayed that way, looking each other in the eyes, holding hands. 

 

He heard someone clear their throat next to them and Dean forced himself to look away from Castiel. Donna’s niece, Wendy, was looking down at him and trying to hold back a smile. “Hi,” she said brightly. “Can I start you gentlemen with something to drink?  Our milkshake special today is Birthday Cake.”

 

Dean made a face. Sounded like something Gabe would sell his soul for. “Do you have the cherry limeade yet?  I know it’s kind of early in the year, but,” Dean trailed off and smiled at Wendy. 

 

“I’m sure that Donna can manage to whip up a batch for you,” she said.  “For you, sir?”

 

“Water, please,” Castiel said. 

 

“With a lemon?” Wendy smiled at him. 

 

Castiel tilted his head and looked utterly perplexed, as though he had never considered the idea of adding something to his water. “Yes?” He said after a long pause, the word lilting as though it were a question. “Thank you.”

 

“Coming right up,” Wendy left. 

 

“Birthday Cake milkshakes,” Castiel shook his head. “My brother would enjoy that.  He has an almost revolting sweet tooth.”

 

“Yeah, I have a friend like that,” Dean commented, briefly thinking of Gabe.  Shaking his head, Dean leaned forward, placing his free arm on the table, uncaringly.   “So,” Dean turned his attention back to his incredibly sexy date. “Cas? Tell me all about yourself.”

 

He was pleased that he wasn’t reprimanded for shortening the man’s name; although he did receive an odd look. Dean was content to simply listen to Castiel speak, giving snippets of information that Dean was filing away in his mind for the future. Because they were  _ damn  _ sure going to have a future!

 

It wasn’t simply the fact that Cas was drop-dead gorgeous, he was also kind and funny and very intelligent—despite allowing himself to be tricked by his brother so easily. Dean was honestly enjoying everything about their date. Cas told him quite a bit about himself, as well as encouraging Dean to open up a bit as well. 

 

Their conversation only halted when they ordered their food.  Dean got his usual ‘Bucking Bronco Burger,’ which had deep fried onions and a generous helping of horseradish on it.  When Cas realized he hadn’t even glanced at the menu, he simply ordered the same. Dean beamed. A hot, funny, smart guy who knew a good burger when he saw it—Dean might actually be in love. 

 

They continued to chat as they ate as well. Dean doing his best to  _ not  _ talk with his mouth full and occasionally failing. Cas seemed the type to frown on such a thing at first, but he would cover his mouth with his hand and still speak through his food. As though simply conversing with Dean was more important than propriety, and Dean’s heart stuttered at the thought. 

 

Dean told Cas about how close he was to Sam, while Cas mentioned that he’d signed up for the dating site at the urging of his older brother. Dean didn’t point out that Cas’ brother had also played a trick on him with the outdated list of chat speak. He didn’t want Cas to be embarrassed, and now that Dean knew the man, frankly, he didn’t care about their first conversation in any way. 

 

Their empty plates were cleared away, and Dean convinced Cas to share some pie with him. Castiel asked for cherry, saying that it was his favorite. Dean was just excited about pie.  They both expressed their satisfaction over dessert with loud moans that drew the attention of a few fellow customers.

 

“I must admit, Dean,” Cas said, placing his fork on the empty pie plate.  “When my brother convinced me to sign up for ‘A Profound Bond,’ I didn’t expect to meet someone such as yourself on the ‘Information Superhighway.’”

 

Dean hadn’t heard the internet referred to in that way for  _ years _ .  He assumed it was another phrase that Cas’ brother had given him. Dean almost wanted to meet this guy, if only to tell him that he was kind of a fucking jerk for messing with someone like Cas. He got the whole ‘brother’ thing, but while he might put shaving cream on Sammy while he was sleeping—he’d never sabotage Sam’s chances for love.

 

“I didn’t expect much from the site either,” Dean said, instead of launching into was a dick Cas’ brother sounded like. “I’m glad I signed up though. You’re my first match,” he paused, unsure if he should continue. “And I’m kind of hoping that you’re my last.”

 

Cas blinked at him. “We hardly know one another,” he finally said. 

 

Dean shrugged. “I guess when you know, you know.”  He caught movement out of the corner of his eye and saw that Wendy was wiping down a nearby table. Dean looked around the diner and realized that they were the only people left. A quick glance at the large clock over the counter showed that the diner was due to close in ten minutes. He and Cas had been sitting in The Matchmaker booth for almost three hours!

 

Dean knew that he needed to do or say something— _ anything _ .  He didn’t want this night to end just yet—he would have to make a move. It might be sort of cheesy and ridiculous, but when the idea flashed through his mind a second later, Dean didn’t hesitate. He pulled up the dating app on his phone and sent a message to Cas.

 

**Impala67: Ask me again.**

 

When Castiel’s phone beeped, Dean waited for his date to inspect it, but Cas seemed to be lost in thought. He cleared his throat a few times before Cas looked up at him, a question in his blue eyes. “Dude,” Dean pointed. “Your phone.”

 

“It can wait,” Cas told him. 

 

“No it can’t,” Dean insisted. “Cas, look at your phone. Please?”

 

It must have been the ‘please’ that did it.  Cas tried to bite back a sigh as he scowled down at his cell. Dean could see the moment Cas read his message, because his expression got even more confused. “Dean, I don’t understand—“

 

“The first thing that you ever asked me,” Dean prompted. “Do you remember?” Cas nodded slowly. “Ask me again, Cas.”

 

Castiel’s head was tilted and there was a deep line between his eyebrows. He seemed to be considering his options, eventually deciding to humor Dean. “Dean.  ‘A/S/L?’”

 

Awe, fuck.  Cas even did awkward fucking quote fingers, and Dean wanted to just pull him into the tightest of hugs.  Instead, he composed himself and smirked at his date. “Thirty-five. Yes, please. And one foot away from you.”

 

Cas shifted in his seat and looked down to his lap. A cloud of self-doubt settled over Dean and he prayed to anyone—or anything—listening that he hadn’t fucked this up. It felt like hours before Cas looked back up and him and their eyes met.  However Cas wasn’t wearing his usual expression that hovered between blasé or confused—he looked predatory. “Yes please?” Cas said, a wicked smile curving his pink lips. 

 

Dean actually felt air punch out of him when hit with the full force of Castiel’s lustful gaze. All he could do in the wake of such intensity was nod.

 

As Castiel requested the bill, Dean remained silent. He finally broke from his stupor and fought over the check. For the first time in his dating life, Dean lost. He blinked stupidly as Castiel paid and then took his hand to drag Dean outside.  Donna and Wendy gave wolf-whistles as they left, causing a light blush on Dean’s cheeks. 

 

Out in the lot, things moved quickly, heating up. Dean let Cas trap him against the door of his car and kiss him fiercely. Usually Dean was the aggressor when it came to sex, but he was losing himself in the feeling of someone else taking charge. The fervent wish that Cas would boss him around a little flashed in Dean’s mind.  He wanted that more than he could imagine. 

 

Cas pulled away, and Dean whined, leaning forward at the loss of those plump lips on his own.  “We should continue this somewhere more private,” Cas suggested. 

 

He vaguely realized that was an excellent point, despite his libido crying out that the backseat of the Impala was private enough.  Dean finally realized what his friends had been telling him all this time—he needed laid! He jerked his head a little toward his car, but Cas shot him down before he even spoke. “We are not doing this in the parking lot,” Castiel’s tone was domineering and firm. It made Dean shiver. “I wish to take my time with you, Dean.”

 

When Cas suggested his place, Dean was more than happy to agree. Apparently it was very close, since Cas had walked to the restaurant, and Dean was in favor of somewhere nearby. They took the Impala, since Dean refused to leave her in a parking lot alone. Castiel hadn’t been kidding when he said his place was down the street because it took less than two minutes to drive there. 

 

They pulled up to the curb and got out, their hands immediately grabbing for each other.  Cas was pulling Dean up the walkway, their lips tasting eagerly as they tripped up onto the front porch. As Cas rummaged for the key, Dean managed to blink himself out of his lusty haze. “You don’t live here,” Dean said. 

 

Castiel tilted his head inquisitively and shoved the key into the lock. It clicked open. “I beg to differ,” he said. 

 

His mouth dropped open and Dean knew that he looked utterly shocked. “This is my brother’s house!  I  _ know _ you don’t live here!”

 

Cas blinked at him. “Sam is your brother?”

 

“Yes!” Dean shouted. “How do you know Sam?  What the fuck is going on? I’m pretty sure that Sammy would mention if—“

 

“Gabriel is  _ my  _ brother, Dean,” Cas interrupted. “I mentioned that I had recently moved to town,” Cas waited for Dean to nod. “Gabriel and Sam were kind enough to offer me their spare room until I can acquire a place of my own.”

 

“That tiny little ass—“ Dean was cut off by a firm kiss.

 

When Cas’ lips left his minutes later, Dean knew that he looked needy—because he was. He watched Cas through half-lidded eyes as the other man brushed his thumb over Dean’s jaw.  “Please come in with me,” Cas requested. 

 

Dean nodded. Castiel leaned in for another quick kiss before pulling Dean gently through the door and into a house that Dean knew almost as well as his own.  They kicked off their shoes, (Sam’s weird rule), and moved through the small house to the living room at the back. When they stepped inside, there was an odd shape on the couch, silhouetted by the bluish light of the television. Cas clicked on the light, and Sam and Gabe froze from where they were busy making out on the sofa. 

 

“Oh, hey!” Gabe chirped from the couch where he was shirtless and perched on Sam’s lap.  His eyes darted between Dean and his own brother. Sam’s mouth was open and he looked incredibly humiliated at being caught in such a state.  Gabe grinned, “You two finally met, F-Two-F, I see!” He flinched when Sam smacked him and hissed something. “Sorry. I’m not supposed to speak like that because  _ some people _ find it annoying.”

 

“You knew that I was going to meet Dean, didn’t you?” Cas stared at his brother.  Dean was impressed, because he was doing his best to look absolutely  _ anywhere  _ that wasn’t _ his _ brother and Gabriel doing  _ something  _ on the sofa. 

 

“We were aware,” Gabriel smiled. 

 

“Wait,” Dean perked up at the use of ‘we.’  “Sammy knew too? For how long?”

 

“Well, I’ve known since I saw the screen name of the guy you were matched with.  So did Samshine.”

 

“To be fair, I didn’t actually know until after you’d went home that night and Gabe laughed about it for twenty minutes,” Sam piped up. 

 

“Wow.  Awesome.”  Dean pointed at them both. “You two are jerks.”

 

Gabriel ignored him and said brightly, “Are you staying the night, Dean Machine?”

 

Before Dean could either answer or berate Gabe for another obnoxious new name, Cas spoke for him. “Dean will be spending as many nights here as he wishes.”

 

“Cool,” Gabe said. He immediately bent his head and started sucking kisses into Sam’s neck without another word. 

 

Dean shuddered, especially when Sam let out a moan. He didn’t protest when Cas took his hand and led him upstairs and into his room. Thankfully, there weren’t any sounds once the door was closed behind them. “I can’t believe those two!” Dean said. 

 

“Are you truly surprised?” Cas raised an eyebrow. “You’ve known my brother for years.  It’s also clear to me, that despite being rather mature, Sam  _ does  _ allow Gabriel to bring out his more playful side.  I’m sure they thought it was rather funny.”

 

“It was a dick move,” Dean said. Cas stared at him until he sighed. “Okay, so  _ maybe  _ in a decade it will be funny to me too.”

 

A harsh shout echoed through the floor from below and Dean rolled his eyes. Awesome. He was going to get to listen to Sammy get laid. He looked over at Castiel who had a wicked glint to his eyes. “Dean?” Cas said, moving toward him with powerful grace. “Would you care to join me in showing our brothers how amazing sex  _ really _ sounds?”

 

Oh fuck yes!  Dean practically jumped into Cas’ arms as their lips crashed.  His front teeth bumped painfully against Cas’ and they both grunted and readjusted as quickly as possible.  Dean’s hands were moving of their own volition, yanking at Castiel’s tie. He had just started to work on pulling off the bulky trenchcoat when Cas moved quickly and slammed Dean backwards into the closed door with a thud. 

 

It didn’t hurt. In fact, it was downright sexy. Cas’ strong hands were gripping Dean’s shoulders keeping him in place. Cas pulled away long enough for their eyes to meet and Dean nodded, licking his lips. Cas moved in, running his tongue along Dean’s jaw before moving down and suckling at the thinner skin of Dean’s neck.  When Cas stopped, Dean actually whimpered. “I’m going to mark you, Dean,” Cas hummed against his neck. “I’m going make sure that everyone who sees you, knows that you belong with me.”

 

The feeling of those kiss-swollen lips brushing his neck before suckling deeply made Dean’s eyes flutter shut. His head fell back, knocking against the hard wood of the door.  “Yeah, Cas,” Dean was breathless, his hands running down Castiel’s muscled back, trying to bring the man as close as possible. “I want everyone to know,” Dean babbled. “Mark me up, make me yours!”

 

Cas didn’t respond verbally, but his mouth was moving and his hips were rubbing insistently against Dean’s hardness.  Pushing back, Dean groaned as he felt the thickness of Castiel through his slacks. Cas gave a throaty growl and one of his hands fisted roughly in Dean’s hair. Fuck, this was exactly what he wanted—what Dean  _ needed _ .  He felt an overwhelming urge to beg. To ask Cas to take care of him in any way that he could. 

 

In an instant, Castiel was gone and Dean’s eyes snapped open. The tie that he’d been working on was being jerked off of Cas’ neck as the other man watched Dean. Their eyes were locked, Dean leaning against the door, his fists clenching and his chest heaving. The look that Cas was giving him was something straight out of his deepest fantasies. The ones where a powerful man did what he wished to Dean—making the normally dominant man a writhing, needy, mess.

 

He could feel precum leaking from his aching cock as it pressed into his zipper.  That was going to stain. Through the haze, Dean reached to unzip his jeans, wanting the naked part to come faster.  Cas raised a single eyebrow which was enough to give Dean pause. In an instant Cas was on him, gripping Dean’s wrist. The touch was gentle enough to be painless, but the intent was crystal clear—No. Cas didn’t even have to say it. 

 

“Allow me,” he whispered into Dean’s ear, undoing the unbearable tight pants, while Dean simply watched, his mouth hanging open. “May I touch you, Dean?”  A nod. “Use your words please,” Cas requested. 

 

“Yeah,” Dean gasped. “Please touch me, Cas.”  The other man eyed him long enough that Dean squirmed and found himself shamefully biting his lip like a fucking virgin.  “I can’t—I need— _ Cas _ ,” he finally broke. “You gotta touch me, man!”

 

Without a word, but with a slight quirk of those pink lips, Cas slid his hand into Dean’s open pants and under the elastic of his underwear. Cas’ touch was warm and confident. He circled his palm around Dean’s dick, which throbbed at the contact. Dean himself groaned, long and low.  When he moved his hips, trying to push himself further into Cas’ grip, his lover leaned close and called him a ‘very naughty boy,’ and Dean almost came right then. 

 

“I have so many things I wish to do to you, and  _ for  _ you, Dean,” Cas’ lips tickled the shell of his ear. “But tonight, I just want you to scream for me. Can you do that, Dean?  Can you be a good boy and scream so loud that everyone hears how lovely you feel?”

 

_ Oh, Fuck! _  Dean was worried that he was going to come all over Cas’ hand—and the man wasn’t even  _ doing _ anything. His hand was gripped around Dean’s dick, just enough pressure to feel good—but anytime that Dean moved, he was quickly shut down.  He nodded quickly and said, “Yeah, Cas. I can be a good boy.”

 

He received a few slow strokes to his cock for his response.  “Excellent,” Cas gave one more slide of his hand and then a slight squeeze before moving away. “You’re going to remove all of your clothes and then get onto the bed.  I would like you up near the pillows on your elbows and knees.”

 

Dean’s eyes were wide and his mouth went dry. It was as though Cas was reading his mind—saying everything that Dean had always wanted.  He found that he was silently nodding along as Cas continued. “You may use the headboard to brace if needed, but you  _ will not  _ push back on me at any time. I am going to be in control of your pleasure.  Do you understand?”

 

“Yes,” Dean said on a swallow. 

 

“Don’t keep me waiting,” Cas’ voice was slightly playful for the first time since they’d returned to the house. He gave Dean a light swat on his butt, causing the muscles to jiggle.

 

It would have been embarrassing at how quickly Dean complied, if he hadn’t been so achingly horny. Castiel’s words and touches had ticked every single one of Dean’s boxes and he wanted this again and again.

 

His clothes piled onto the floor, and as he pulled his pants the rest of the way off, he noticed Cas getting out condoms and lube from the dresser.  A sharp glance from those piercing blue eyes had Dean picking up the pace and almost jumping on the bed in anticipation.

 

He was on his knees, his face almost buried in the pillows, palms pressed on the headboard—waiting. The first light touch of Castiel, the man’s fingers grazing the skin of Dean’s rounded butt, was a special kind of torture. Dean wanted more, so much more. “You look beautiful, Dean,” Cas said softly—and if that didn’t make Dean want to smile.

 

Behind him, the bed dipped as Cas climbed on, settling behind him. Dean twisted his neck and tried to look behind him.  Fuck, Cas looked so damn sexy! While Dean was fully nude and exposed, Cas was still wearing his slacks, his shirt open, exposing a firm chest, his tie dangling around his neck.  If it was possible for his dick to get harder, then it happened when Dean caught a glimpse of his lover. 

 

“Dean,” Cas’ palm was resting on the small of Dean’s back, pressing lightly, just enough to bow his spine. “I would like to open and prepare you with my hand.  And then I would very much enjoy fucking you into the mattress until you come. May I please do those things, Dean?”

 

“Oh, yeah, Cas!” Dean groaned and tucked his face back into the pillow. “Yeah, I want that too!  Please, Cas! I need you to fuck me!”

 

“Patience, Dean.”  He could hear the smile in Cas’ voice. 

 

The cap of the lube snicked as Castiel opened it. Dean tried to stay still, the way Cas had requested, but the man was taking  _ way _ too long and Dean accidentally wiggled his hips. Just barely, but enough to be noticed. “If you keep teasing me, I will be forced to punish you,” Cas told him. That only made Dean push his butt back toward Cas and give a little moan. “I think you would look so beautiful with a bright red ass, Dean.  Would you enjoy that? If I spanked you red and then fucked you hard?”

 

“Oh fuck, yes!” Dean actually shouted. “Please, Cas!  Spank me, Angel!” He taunted once more with his hips and a hand came down sharply, just once. It stung horribly and Dean’s mouth popped open.  “Yes!”

 

“You really are so naughty, Dean,” Cas said. “But I don’t have the patience to punish you properly tonight. I need to feel what it’s like inside your tight body.  But mark me—I  _ will _ have you over my knee sometime very soon.”

 

The spot where Cas’ hand had struck was still tingling when Dean felt a cool, slick finger rubbing his hole. There was just a slight press, enough that Cas’ digit began to push into him.  He tried  _ so _ hard to stay still, but he wanted so much more. He grunted a little and begged, “Cas.”

 

His request was granted and the rest of Cas’ finger slid into him, making lazy circles.  Every so often it would barely nudge that perfect spot that Dean craved. “You’re somewhat prepped already, aren’t you?”

 

Dean nodded, unable to find the correct words. He hadn’t had time to pregame after work that evening, but he  _ had  _ set his alarm half an hour early so that he could have a little fun before the day began. In anticipation of possibly getting laid, Dean had used one of his favorite dildos before stumbling to the shower to clean up before work.  He was more loose than he would have been without the toy’s help.

 

A wave of nerves swept over him as Cas pushed another finger in.  Sure, he’d had years with his toys, countless fantasies about his ass being fucked raw, and the night with Bela—but he had never  _ actually _ been with a man. The thoughts of what his family would think never even came to light—he’d made peace with that years ago. Dean’s worries were in an entirely different place. What if he sucked at this?

 

Castiel’s fingers were scissoring inside of him and it burned, but felt so perfect. One of them pressed deep, curling into his prostate and Dean gasped. “You are so amazing, Dean,” Cas murmured, as though he could feel Dean’s anxiety. “So sexy, so perfect for me. I can’t wait to be inside you.”  And just like that, Dean relaxed. This is what he’d wanted for so long, and it was finally happening. With a fucking  _ hot  _ man as well. 

 

One of Dean’s hands fisted, and he gasped as the third finger entered him.  The sensations were almost agonizing in their pleasure. Someone else—a  _ male _ someone—was finally touching him in the intimate ways that he craved.  “Cas! I need you! You gotta—you—Cas!”

 

“You’re still a little tight,” Cas’ fingers pushed deep. 

 

“Don’t care,” Dean moaned and shoved backwards into Cas’ hand. “Need you!”

 

He got another sharp spank to his ass for the motion. Dean gasped, remembering that Cas had instructed him to not push back.  “Sorry,” he mumbled. 

 

Cas slowly removed his fingers and Dean made a small, angry sound. “If you insist on being naughty, Dean,” Cas said. “Then I might have to fuck you until you behave.”

 

Oh,  _ fuck yes _ !  Dean needed that. He wanted to feel Cas. He wanted to cry out the other man’s name and have his ass plowed until he was hoarse from screaming and spent the next week feeling it.  There was the crinkle of a wrapper, and Dean knew that Cas was finally putting a condom on to fuck him. He sort of wanted to sob with happiness. 

 

The bed shifted as Cas moved closer to him. Those strong hands rested on each cheek and spread, exposing Dean’s willing hole.  He wanted to move—God, Dean wanted to do  _ something _ , but he knew that he shouldn’t. Cas’ fingers were massaging his butt, squeezing and moving, spreading him. “Cas, I—“

 

“I know what you need, Dean,” Cas said. And then the tip was pushing into him.  

 

Dean’s breath caught and he managed a soft, “Oh!”

 

“Now remember,” Cas paused. “I want you to scream. I want to hear how much you love being fucked, Dean.” All Dean could do was nod. 

 

Cas moved just barely and slid in further. His cock was thick, much thicker than Dean’s largest toy. He had never felt so split.  His asshole burned with each movement and a small sound escaped Dean’s lips. Immediately, Cas stopped, which only made Dean whine more. “Are you all right?”

 

“So fucking big,” Dean managed. “It’s so much.”  Thankfully, Cas didn’t pull out. He just stilled, his hands rubbing Dean’s butt cheeks soothingly.  Impatiently, Dean shifted his weight on his knees and his muscles gave Cas a little squeeze, drawing a beautiful sound from the man behind him. “You can do it,” Dean’s voice was muffled. He’d buried his face into his arms and the pillow. 

 

“I don’t want to hurt you,” Cas said. 

 

“You won’t,” Dean promised. “I’ve just never had anything so big.”  He paused. “You feel so good, Angel. Please fuck me.”

 

Cas didn’t say a word, he simply began to push once more.  The guttural moan that poured from Dean’s mouth when Cas shoved in another inch was long and loud.  “Your body is so perfect,” Cas praised. “Your ass feels amazing, so hot and tight for me. Oh, Dean!”

 

The last few inches pushed into him and he felt Cas’ pelvis bump him, the zipper of his pants scraping Dean’s skin..  He felt so completely full. Cas was giving him everything. His fat cock was shoved up Dean’s ass, and it was the best thing that had ever happened to Dean Winchester. His hands were gripping into the pillows at the sensation, and Cas wasn’t even moving yet.

 

He groaned Cas’ name, dragging the word out and finally Cas began to move. The slow slide of Cas inside of him had Dean moaning and pushing into the mattress.  One hand shot out and braced on the headboard, the other was gripping the blanket so tight that Dean worried he may rip it.

 

Cas was moving deliberately. It was a steady pace, and it was too slow for Dean. He wanted to  _ feel _ this!  He wanted the sting and the burn. He wanted to remember Cas each time he moved for the next week.  Dean felt hands move from his hips and rest on his back. Cas pressed down, almost forcing Dean into the bed.  As soon as Dean let it happen, he saw stars. 

 

The new angle allowed Cas to penetrate deeper.  Every few thrusts, Dean would feel the spike of ecstasy from his prostate. He clenched his muscles and received a growl and a hand suddenly pulling at his hair for his efforts. The girth of Cas’ cock was gradually easier to take, and the more relaxed Dean became, the more forcefully Cas fucked him.

 

Each snap of Castiel’s hips rocked him, and Dean’s mouth fell open. He could hear someone screaming—yelling Cas’ name along with ‘Please’ and ‘More.’  It took a moment before he realized that it was  _ him _ . Cas was actually making him scream. Dean couldn’t have held back his voice even if he’d wanted to. He felt so fantastic—loose and coiled all at once. It was freeing and perfect and Dean never wanted it to end. Why had he waited so long to take a lover after Lisa?  

 

As though Cas knew his thoughts, Dean gasped and shouted, “Fuck,” as a harsh thrust stung his hole. Apparently he liked a little pain, because he immediately begged for more. The fingers in his hair tugged, coaxing Dean’s face out of the pillows. He moaned openly as another slide of Cas’ wide cock banged into his prostate. “Are you going to be a good boy for me now, Dean?” Cas’ tone was rough, on edge. “Are you enjoying how I fuck your tempting little ass?  Am I filling you up the way you like? Tell me, Dean—I want to hear how much you love my cock.”

 

“Cas!  Fuck, Cas, I love your cock!” Dean shouted. He honestly didn’t care if anyone heard, because at the moment, he felt amazing.  “Love how you fuck me, Angel! I love how you pound me with your fat cock—please, Cas, harder!” As Cas fucked into him, Dean started to babble. He had no clue what he was asking for, only that he wanted it harder, deeper, faster, now!

 

The hand on his lower back had moved and was now pushing against his shoulder, holding Dean down. He wiggled just a little, but Cas was much stronger than Dean had originally thought. He could feel the sharp roll of Cas’ hips as he rammed his cock into Dean’s warm body.  The familiar pressure was building in his sac and his own rock hard dick. “Cas, I’m going to come, Angel? Can I come please? Come on your big dick?”

 

Cas grunted, his hips snapping. “Yes, Dean,” Cas groaned. “Come on my cock like a good boy.”

 

With permission secured, Dean titled his own pelvis, allowing for Cas to slam into that perfect spot inside of him. He cried out, calling Cas’ name. “Fuck, Castiel!”  

 

He release was quick and powerful.  Thick, hot jets of cum shot from his untouched cock. In his frenzied release, Dean was rutting the air, with jizz dribbling out of him as Cas still used his now stretched hole.  He tensed as he came, squeezing Cas’ cock as it moved inside him. “I’m almost there,” Cas promised him. Dean didn’t care. He was riding so high—he’d never come that hard, not even with his toys. 

 

When he finally stopped, only a few dribbles slipping from his slit, Dean relaxed into the bed.  Cas was now pushing his shoulders flat out into the mattress, holding him down and riding him furiously. It still felt so good. Dean’s own dick gave a somewhat interested twitch, and that made his eyes fly open in surprise. “You’re so good, Dean,” Cas choked.  “So good for me.”

 

Dean grunted in response. He felt weightless and so satisfied. He was already thinking about when they could do this again—and Cas wasn’t even done. Even as the thought flew by, Dean felt nails dig into his shoulders lightly as Cas stilled above him. He could feel warmth as Cas came, filling the condom.

 

He figured that when they finished, that Cas would pull him close, maybe cuddle, but apparently not. Before Dean could speak, Cas was sliding out of him and Dean gasped at the empty feeling. He’d never felt so perfect or full before, not even with his toys. He missed Cas buried inside of him and it had only been a few moments. 

 

Laying on his stomach in a mess of his own semen, Dean couldn’t bring himself to move.  He turned his head and watched as Castiel pulled off his pants and the shirt that had been hanging off of his body.  The man hadn’t even undressed to fuck him. Perhaps Cas had been just as eager as Dean to have sex. It was sort of a hot concept, and Dean wished that he could have seen what Cas looked like, half dressed and fucking him raw.  It had to have been one of the sexiest things imaginable. He watched as Cas left the room and sighed. His new lover came back less than a minute later, and Dean hummed happily. Cas stroked Dean’s arm and whispered, “Roll over, sweetheart.”

 

Dean could hardly comply, but eventually he did. He was greeted with the warm, wet touch of a soft cloth, wiping him down and removing the mess.  He blinked sleepily up at Cas as the other man cleaned him. “That was amazing,” Dean finally said. 

 

“I’ve never felt so close to someone during sex before,” Cas said simply. “You responded to me so beautifully and without treating me as odd.”

 

Dean pushes himself up onto his elbows and wrinkled his nose. “Why would I think you’re odd?”

 

Cas prodded him until he forced himself to stand so Cas could pull off the soiled blanket. “Most men, such as yourself, do not wish to be...dominated...in any way.”

 

“Not me!” Dean blushed at how eager he sounded. 

 

“I noticed,” Cas actually chuckled a little. He gestured to the bed and tugged Dean with him under the sheet.  “I enjoy maintaining control with my partners, and I also am more attracted to men equal or above my physical stature. Even those who claim to be submissive sometimes balk at the shorter one ‘bossing them around.’”

 

“You’re like, an inch shorter than me—maybe two?  I don’t see the problem,” Dean snuggled into Cas’ body as the other man’s arms wrapped around him. “I kind of always knew I... _ liked _ things like that—I just didn’t know how much.”  He considered if he should say what he was thinking for a moment before decided that he might as well. “When you said you wanted to spank me,” he trailed off and glanced over to Cas. 

 

The damn man was smirking at him. “I believe I mentioned spanking you until your ass was red and then fucking you that way,” Cas reminded him. 

 

Dean groaned and reach to press his palm into his cock. He was getting turned on again, but he knew that his ass couldn’t handle another pounding tonight.  He squeezed his eyes shut and nodded. “Yeah, that,” he was breathless. “I really want that Cas. I want that so much. I bet it would feel so good if you spanked me that hard.”

 

Cas’ arms tightened around him as he leaned in and placed the softest kiss to Dean’s cheek. “I’d be happy to do that for you, Dean.”  His eyelids fluttered closed at the words and the tender gesture. “Sleep,” Cas smiles into Dean’s hair as he nuzzled him. “We can talk more tomorrow.”

 

The room was silent for a full minute before Dean snorted and said, “I bet Sammy and Gabe are bordering on traumatized right now.”

 

“Sam most likely is, yes,” Cas agreed. “I’m less sure about Gabriel.  He would more likely be ‘proud of us,’” Cas used the quote fingers again, which made Dean laugh. 

 

“Well, whatever,” Dean snuggled closer to Cas.  “Serves them right for messing with us.”

 

“If their underhanded ministrations helped to ensure a relationship between us, we’ll never hear the end of it,” Cas pointed out. 

 

Dean groaned, knowing that Cas was right. “Tomorrow,” he said finally. “We can deal with everything tomorrow.”

 

As Dean drifted off to sleep, he felt the ghost of a kiss on his head and heard whispered words. What he thought had been spoken, Dean knew was impossible. They had technically just met that night. But it didn’t stop him from hoping that he had heard correctly. 

**Notes for the Chapter:**

> Hold on for a hot second and I'll have the third (and final) chapter up soon.


	3. ILY

**Notes for the Chapter:**

> I'm posting this one right away because its the last chapter and its really short, so I figured I would just finish this one out.

The next morning dawned, a thin strip of sunlight poking through the curtains and hitting Dean directly in the eyes. For the first time in a while, he wasn’t waking up with a hangover and it was sort of amazing. The fact that strong, warm arms were curling around him and a thick, half-hard dick was nestled between his ass cheeks was simply a _bonus!_ Humming with pleasure, Dean wiggled around both to face his lover and also to get the damn sun out of his face.

 

He pressed a lazy kiss to Cas’ lips and received a a rather enthusiastic response considering that his partner was still half asleep. Castiel didn’t even open his eyes when he said, “Good morning, Dean,” in that low rumble. It sent a fucking shiver down Dean’s spine.  He leaned in for another kiss, thinking that _this_ was the perfect way to wake up.

 

Suddenly, Dean shot straight up in bed as the door to Cas’ room flung open and Gabriel poked his head inside. “You two are really fucking loud, you know that?”

 

“Morning, Dean!” Sam’s laughing voice called out from the hallway and Dean wanted to bury himself into the pillows and die.

 

“Please leave,” Cas’ tone wasn’t very polite as he growled from under the blanket.

 

“Sure,” Gabe winked.  “Hurry up though—Samshine and I are taking you two out for waffles.  Up and at ‘em, Cassie!”

 

He slammed the door shut as Cas threw a pillow at him. Dean could hear Gabe laughing as he walked downstairs.  “I know that I said I wanted to punish them for interfering last night,” Dean groaned. “But now that I’m awake, I realize that it was a terrible idea.”

 

Cas made a noise of agreement before unceremoniously throwing off the covers and dragging himself out of bed. “We should get ready,” he said.  “If we take too long, Gabriel will likely come back and spray us with water from his squirt gun.”

 

“I hate that thing,” Dean grumbled, remembering the last Fourth of July when Gabe had got him between the eyes while Dean had been manning the grill.

 

The threat of a stream of water in the eyes was enough to get Dean going as well. He borrowed deodorant and clean clothes from Cas—as well as some toothpaste that he used with his finger.  They met Sam and Gabe downstairs within seven minutes. Despite their rushing, Gabe pretended to be annoyed and tapped his foot obnoxiously until they all tumbled out the front door.

 

When they rolled into Donna’s once again, this time bleary-eyed and hankering for coffee, Donna smiled at him and whispered, “Still together the next morning!  I told you that The Matchmaker was going to work!”

 

“You were right, Donna,” Dean smiled as she sat the four of them in a large booth by the window.

 

“Awe, you gave them The Matchmaker?  Donna, darling—how could you?” Gabe groaned. “No wonder they kept us awake all night!  They had magical love juju going on.”

 

“Donna, you never let Gabe and I sit in The Matchmaker,” Sam pointed out as he scooted in the seat next to his boyfriend.

 

“No I don’t,” Donna said, handing out menus. “You two already know you’re perfect for each other—you don’t need the extra push.”  She paused and smiled slyly at Sam and Gabriel. “One of you is going to have to bite the bullet and propose on your own. Because I’m not helping, and you both know it’s the right thing to do.”

 

Dean snickered as his brother and Gabriel blushed at her words. He also noticed that they were refusing to let go of each other’s hands. Donna was right—his baby brother was _definitely_ heading toward the altar with his snarky little lover. Dean glanced at Cas, his mind rolling with the idea that marriage suddenly sounded like a good idea again.

 

Well—what do you know.

 

They ordered with Wendy and the talk turned to how Cas was settling in to his new town, which Dean was grateful for.  He didn’t want to deal with more teasing this early--who knew what Gabe would come up with? When Wendy came back with their food, she made a pointed comment about Dean and Castiel and the fact that they’d been in The Booth the previous evening. Much to Dean’s chagrin, another round of teasing began again as she walked away and they began to eat.

 

“Speaking of marriage, Cassie,” Gabe wiggled his eyebrows, and pointed to his brother with his fork.  “Sure _sounded_ like you and Dean-o hit it off last night.”

 

“No thanks to you,” Cas said pointedly.

 

Gabe put his hand on his chest dramatically.  “You’re hurting my feelings.”

 

“I am not.”

 

“I might not recover.”

 

“Gabe,” Sam cut in, and Dean could see his brother grab the man’s thigh. “You’ll be fine.”

 

“If you say so, kiddo,” Gabe turned to Sam.  “A kiss would really ease the pain of my brother being so mean to me.”  Sam rolled his eyes, but still gave in and pressed a sweet kiss to Gabriel’s lips.

 

“You taste like syrup,” Dean heard Sam whisper. Ew. He didn’t need to watch the kissing and adorable whispering—not when it involved his little brother.  He cleared his throat and glared at his friend.

 

“I’m not being mean,” Castiel said once their brothers broke apart. “You gave me that list—and everything on it was from the nineteen-nineties!  I looked it up.”

 

Gabe didn’t even flinch. “Yup.”

 

“Were you _trying_ to make me look unintelligent to potential partners?” Cas sighed, and Dean had the feeling that he was less angry, and more resigned. Cas had most likely been dealing with Gabriel and his...Gabrielness forever. Dean liked Gabe—they were friends—but a lifetime of Gabriel Novak sounded daunting at best. Suddenly, Dean was slightly concerned for Sammy.

 

“No!” Gabe actually looked slightly offended. “I didn’t want you to look dumb.”

 

“Well, I felt dumb,” Cas said, his voice just on the edge of a pout.

 

“It _was_ kind of mean,” Sam told his boyfriend.

 

Dean glared. “So not only did you know that we were meeting each other, you knew that Gabe had messed with Cas?”

 

“Sorry,” Sam looked chastised.

 

“I don’t mind, Dean,” Cas told him. “While I’m sure that Sam and I will eventually be good friends, he has no current obligation to inform me of Gabriel’s...assbutt tendencies.”

 

“I had a very good reason for doing what I did,” Gabe spoke up. He looked unusually serious for a split second before smirking. “You looking dumb was just a happy byproduct.”

 

“I hate you.”

 

“No you don’t,” Gabe shot back.

 

“Why would you do that to him, Gabe?” Dean sighed with exasperation at his friend.

 

Gabriel leaned back in the booth and grinned at both of them while throwing his arm over Sam’s shoulders. “It worked, didn’t it?  You should both thank me.”

 

“What worked?” Castiel was now eyeing his brother.

 

“Cas,” Gabe leveled him. “I love you, you know that. But you’re...not entirely normal.”

 

“I am aware,” Cas grumbled.

 

Dean pulled his new lover to him and shot a look at Gabe. Before he could start yelling, Gabriel held up a finger and kept speaking.  “I gave you those outdated chat room acronyms because it would immediately make it known that you were a bit weird. I figured that if someone still wanted to meet up with you, that you’d be golden!”

 

“Really?” Cas looked pensive and Dean wrinkled his nose.

 

“Of course!” Gabe smiled at his brother. “You’re incredibly hot—it runs in the family.” Everyone rolled their eyes at Gabe for that comment. “But you’re also smart, and funny in your own way.  And anyone willing to see past the awkwardness and frankly, the staring, would see that you’re a fucking amazing person!”

 

“That’s actually really sweet,” Sam finally said, breaking them out of their silence.

 

“I know,” Gabe looked entirely too pleased with himself. “And I _was_ right, wasn’t I, Dean-o?  Cassie is amazing, isn’t he?”

 

Dean gave Gabe a bitchy look. “Yeah he is.”  He grumbled for a moment before confirming. “You were right, Gabe.”

 

“I’m always right.”  Gabe preened for a second before a piece of syrup soaked waffle hit him in the face. “What the fuck?” Gabe’s mouth hung open, staring at his brother who was snickering behind his hand. “Cassie!  You saucy little jerk!”

 

“Serves you right,” Cas said sanctimoniously, once he’d stopped laughing. “Next time, don’t help me pick up men. I’ll handle it on my own.”

 

“Angel,” Dean leaned in and growled into Castiel’s ear. “There’s not going to _be_ a next time.”

 

“That sounds permanent, Dean,” Cas said.

 

He could feel three sets of eyes on him as Sam and Gabe listened in. “Good,” Dean said. “It’s meant to be permanent. You and me,” Dean smiled. “It’s kind of feeling like forever.”

 

“Do you mean that, Dean?” Cas’ voice was so hopeful, and it filled Dean with emotion.

 

He nodded. Because for the first time in three years, Dean Winchester was thinking about something good—something beautiful for the future.  He no longer associated the idea of marriage with a woman who couldn’t be faithful. For the last twelve hours, when Dean thought of forever, he pictured sleepy blue eyes and pink lips kissing him awake every morning. He heard a grave voice saying, “I love you, Dean,” each night. Yeah.  Dean meant it. He really did.

 

“What do you say, Angel?  It’s been a few hours—seems like long enough,” Dean took a deep breath.  He could see Sammy’s shocked expression, Gabe’s smirk and Cas’ desire. “Marry me?”

 

“Yes, Dean.  I am ‘thirsty’ for that outcome,” Cas did more quote fingers.

 

“What the fuck?” Gabe broke in. “I didn’t teach you that one!”

 

Cas leveled his brother with a look.  “I google searched it.” He looked back at Dean.  “I believe I used it correctly—thirsty. Meaning I’m excited?”

 

Sam was flat out giggling like a child, burying his face in Gabe’s shoulder. Gabriel was staring at his brother with a combination of pride _and_ horror.  Dean forced himself into a neutral expression at Cas’ attempt at popular slang. Apparently his—now fiancé—was a bit of a dork in any decade. Dean wouldn’t have it any other way.

 

“Yeah Cas,” he smiled, shaking his head fondly. “I’m ‘thirsty’ for you too, Angel.”

 

Sam and Gabriel gagged behind their hands as Dean pulled Castiel into a passionate kiss.

 

**Notes for the Chapter:**

> Thanks for reading! I hope that you enjoyed it :)

**Author's Note:**

> 🍭I am on Tumblr as crowley-loves-usuk if anyone feels the urge to follow or message me. I love talking to readers! 🍭


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